GB1430816A - Process for the preparation of 6,7-benzomorphan derivatives and intermediates useful therein - Google Patents

Process for the preparation of 6,7-benzomorphan derivatives and intermediates useful therein

Info

Publication number
GB1430816A
GB1430816A GB5039573A GB5039573A GB1430816A GB 1430816 A GB1430816 A GB 1430816A GB 5039573 A GB5039573 A GB 5039573A GB 5039573 A GB5039573 A GB 5039573A GB 1430816 A GB1430816 A GB 1430816A
Authority
GB
United Kingdom
Prior art keywords
formula
phenyl
amino
alkyl
hydrogenolysis
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB5039573A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
KH Neochem Co Ltd
Original Assignee
Kyowa Hakko Kogyo Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP10905472A external-priority patent/JPS537431B2/ja
Priority claimed from JP47108408A external-priority patent/JPS5234613B2/ja
Priority claimed from JP10840972A external-priority patent/JPS533396B2/ja
Application filed by Kyowa Hakko Kogyo Co Ltd filed Critical Kyowa Hakko Kogyo Co Ltd
Publication of GB1430816A publication Critical patent/GB1430816A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/22—Bridged ring systems
    • C07D221/26—Benzomorphans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1430816 Tetrahydronaphthalene derivatives; benzomorphan KYOWA HAKKO KOGYO CO Ltd 30 Oct 1973 [31 Oct 1972 (3)] 50395/73 Heading C2C Novel 2 - amino - 1,2,3,4 - tetrahydronaphthalene derivatives of the Formula (III) wherein R 1 is H, OH, alkyl, alkoxy, benzyloxy or acyloxy; R 2 is H, alkyl, cycloalkyl, cycloalkylalkyl, alkenyl, haloalkenyl or alkyl substituted by any one of the following; phenyl, benzoyl, keto-oxygen, or a group; R 3 and R 4 are each alkyl; Y is alkoxy, phenoxy or benzyloxy; and R 5 is H, benzyl or other organic blocking group removable by hydrogenolysis; may be obtained by subjecting a 1-phenyl-2-amino-3-hexene of the Formula (V) in which R 2 and R 5 are other than H, to ring closure, the tetrahydronaphthalene obtained optionally being subjected to hydrogenolysis to replace either or both of R 2 and R 5 by H. 6,7-Benzomorphan derivatives of the Formula (I) in which R 1 to R 4 are as above, are obtained by subjecting a compound of Formula (III) above to ring closure and optionally removing an organic group R 5 by hydrogenolysis. Ring closure may be effected by treatment of (III) in an inert solvent with a hydrogen halide, or a Lewis acid. The intermediate 1-phenyl-2-amino-3-hexene (V) may be obtained by dehydration of a corresponding hexanol (IV) which is itself obtained by reacting a 1-phenyl 2 amino-3-hexanone of the Formula (II) with an organo metallic compound R 3 CHXCH 2 CH 2 Y (where X = Li or Mg halogen)
GB5039573A 1972-10-31 1973-10-30 Process for the preparation of 6,7-benzomorphan derivatives and intermediates useful therein Expired GB1430816A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP10905472A JPS537431B2 (en) 1972-10-31 1972-10-31
JP47108408A JPS5234613B2 (en) 1972-10-31 1972-10-31
JP10840972A JPS533396B2 (en) 1972-10-31 1972-10-31

Publications (1)

Publication Number Publication Date
GB1430816A true GB1430816A (en) 1976-04-07

Family

ID=27311224

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5039573A Expired GB1430816A (en) 1972-10-31 1973-10-30 Process for the preparation of 6,7-benzomorphan derivatives and intermediates useful therein

Country Status (5)

Country Link
US (1) US3969468A (en)
CA (1) CA1010031A (en)
DE (1) DE2354327C3 (en)
FR (1) FR2210611B1 (en)
GB (1) GB1430816A (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1513961A (en) * 1975-02-25 1978-06-14 Acf Chemiefarma Nv 6,7-benzomorphans method for their preparation and intermediates
JPS5919542B2 (en) * 1976-06-24 1984-05-07 旭電化工業株式会社 Benzazosine derivative
US4208523A (en) * 1978-11-30 1980-06-17 Sterling Drug Inc. 11-Lower-alkyl-, 11-phenyl-lower-alkyl- and 11-cyclo-lower-alkyl-lower-alkyl-hexahydro-2,6-methano-3-benzazocines
SE8004002L (en) * 1980-05-29 1981-11-30 Arvidsson Folke Lars Erik THERAPEUTICALLY APPLICABLE TETRALIN DERIVATIVES

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2112899A (en) * 1935-03-09 1938-04-05 Squibb & Sons Inc Derivatives of ac-tetrahydro-betanaphthylamine
US3637740A (en) * 1969-04-21 1972-01-25 Pfizer Aminobenzocycloalkane compounds
US3836670A (en) * 1971-11-19 1974-09-17 American Home Prod Benzobicycloalkane amines for inducing analgesia
US3751420A (en) * 1971-04-01 1973-08-07 Squibb & Sons Inc Monoolmonoene amines

Also Published As

Publication number Publication date
US3969468A (en) 1976-07-13
FR2210611B1 (en) 1976-11-19
FR2210611A1 (en) 1974-07-12
DE2354327A1 (en) 1974-05-09
CA1010031A (en) 1977-05-10
DE2354327B2 (en) 1977-12-08
DE2354327C3 (en) 1978-08-10

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee